Character history

Life until 1998

Antonio "Toni" Cipriani was born to Ma Cipriani and an unnamed father, a member of one of the city's Mafia families, in Portland, Liberty City. He lived with his parents in their home and restaurant located in the Saint Mark's neighbourhood. Cipriani grew up in a Mafia controlled neighbourhood and later became involved in the criminal underworld before joining the Leone Family. In 1994 Toni killed a made man on orders from Salvatore Leone, Don of the Leone Family, and left Liberty City for an unknown destination.

Return to Liberty City

Toni returned to Liberty City on a coach in 1998 and immediately met a grateful Salvatore who immediately places him under the leadership of made manVincenzo Cilli who rose through the family's hierarchy during Toni's abscene.

Toni initially finds himself performing menial tasks for Cilli, including taking a drug dealer to his turf but is later asked to do more troublesome tasks, including assisting robbers escape from the AmCo petrol station. Toni, however, is later set up by Vincenzo when collecting a car loaded with drugs being watched by the police. Toni, angry and ashamed at working for Vincenzo, is entrusted with working for Joseph Daniel O'Toole, a member of the rival Sindacco Family who wants to join the Leones. While working for O'Toole, Toni manages to impress Salvatore by driving him away from Paulie's Revue Bar, which was being raided by the police, by preventing the destruction of a Leone controlled casino and then, in retaliation, destroying the Sindacco run Dolls House casino/bordello.

Toni also confronts his mother for the first time in four years following his hasty departure. His mother, disappointed in his lack of phone calls while in hiding, continually makes negative remarks about his character and appearance, claiming he is too thin. Toni, in attempts to impress his mother, takes photographs of Giovanni Casa in his underwear and chasing two prostitutes (including Mona Lott) and later killing him when he stopped paying protection money, wins an illegal street race and kills Dan Sucho, as well as killing many Triads. His attempts, however, fall short of her high expectations following her husbands example and she places a hit on Toni, asking him to die 'like a real man'.

This occurs, however, only after an argument over comments Toni had supposedly made about Salvatore and his intelligence. The argument involves Salvatore pointing a gun at Toni before realising his loyalty and admitting to becoming increasingly paranoid. Salvatore, in retaliation at the Mayors actions, has Toni kill the Mayor on his jog in Belleville Park, retrieveing his phone in the process. For this, his work for the Leone Family and twice rescuing Salvatore he is made despite his concerns following O'Toole's 'ceremony'.

Working close with Salvatore

During this time Salvatore Leone is arrested and placed in prison on Shoreside Vale. While awaiting trial he visited by Toni, disguised as a lawyer named Lionel, and is told to attack the Forelli and Sindacco families for his incarceration. Toni assists the Southside Hoods in taking control of Wichita Gardens, a Forelli neighbourhood, and then kills Sindacco DonPaulie Sindacco, before attacking a Yakuza weapons storage and destroying their tank.

Life between 1998 and 2001

Toni continued to work for Salvatore Leone and the Leone Family but became less active in the actual criminal activity. During this time he also moved back in with his mother and her restaurant, which he also became more active in running. He put weight on during this time and began to have a shorter temper, likely due to his mothers constant disapproval of him, and is known to have punched a man for claiming the ziti at the restaurant was over-baked. He also comes under investigation by the police for his links to Salvatore Leone, although Toni maintains that he only purchases tomato sauce from him. He also manages, throughout the period, to establish himself as the right hand man of Salvatore, being placed above Salvatore's own son Joey.

Personality

Toni's behaviour changes somewhat throughout his appearances. In 1998, Toni was somewhat easy-going, although very business-oriented and had somewhat of a control of his temper. By 2001, his mother's endless harshness had given him an explosive temper and a very short fuse. Although short-tempered and aggressive, Toni rarely gets angry at his mother, despite her constant insults, and does everything he can to please her. Likewise, Toni had great respect for Salvatore Leone and was extremely loyal to him. Toni is also known for making unfortunate choices, due to his hot temper.

Toni also had a darker side. When enraged, Toni gets extremely violent like when he killed and brutally dismembered Giovanni Casa and sold his cut-up body to Casa's deli. He also seemed generally unfazed by the disastrous attack he performed on Fort Staunton. Despite this, Toni was capable of remorse as he is known to attend church to atone for his deeds.

Toni Cipriani is likely homage of Tony Soprano, the main character from The Sopranos. Aside from their names, both characters also share ongoing problems with their mothers, who also ordered hits on them (which occur to Toni in GTA: Liberty City Stories). Early GTA III game art for Cipriani, however, depicts him bearing a likeness to Joe Pesci.

Toni is the only protagonist to give another protagonist (Claude) missions. (Excluding the three protagonists of Grand Theft Auto V)

The surname 'Cipriani' is a possible reference to the Itailian dish occupying the same name.

Toni Cipriani's appearance changes in between cutscenes and his in-game appearance in GTA Liberty City Stories. In the cutscenes his upper body is more downward a bit chubby, but in the in-game appearance he is shape more muscular.

Until Trevor Philips, Toni Cipriani was the only protagonist who deliberately dismembered a person without the player's control.